Photo by Tim Needles via flickr

You were hired as The New Yorker’s first Web editor in 2006, when NewYorker.com was relatively primitive and “blog” was a four-letter word to most staff writers. How have attitudes toward the Web changed since then?

They’ve changed a lot. We relaunched the site in March 2007 but when I came it hadn’t been redesigned since March 2001. You really couldn’t find anything other than the current week’s content, and even that packaged better would have been more appealing to people. But because of the late 20th-century Web design of it, it was a narrow, dark page.

Some of my job is being the Web evangelist in the office – getting people involved and explaining why the Web is helpful to them and their story. One of the reasons we started the Out Loud podcast was the chance to sit down with someone every week and introduce this stuff to them.

It’s comforting for a writer to know they’re in a magazine with a circulation of 1 million people, but it’s a different thing to be able to chat with 30 people who are engaged in a topic you wrote about last week. And writers who are hesitant to do that end up really enjoying that kind of connection with readers. It’s also a good way of reaching a different audience, people who might want to be reading The New Yorker but have to drive to work.

How has the Web changed the magazine’s content? Are writers encouraged to write pieces that will be shared on social networks? Are editors taught to write SEO-friendly heads?

The only changes you see in the magazine are the digital Eustace Tilley in the front-of-book with a box on the contributors page saying what’s online. We also run Web refers as notes at the end of a piece. We leave the headlines on our pieces but we use more SEO-friendly page titles. Not necessarily Digg-style page titles – just straightforward page titles with the proper nouns that refer to what’s in the story.

So no Top 10 lists or other “link bait” stuff?

Well, David Remnick did a long piece about jazz DJ Phil Schaap in the magazine, and wrote a list of his favourite jazz albums for the website. We called it “100 Essential Jazz Albums” – and that got a lot more clicks than his article.

We also did a contest on our books blog called Critterati, encouraging people to dress up their pets as their favourite literary character. We’re aware that people like looking at pictures of dogs and cats on the Internet but if we threw all our energies into this stuff we obviously couldn’t support the kind of journalism we do. You can’t send someone to Rwanda for a month on the kind of revenue earned from pictures of cats!

But fundamentally, The New Yorker is something you want to sit with and not be distracted by. I don’t mean this in a spiritual way, but it’s a meditative experience. The Web is fundamentally a distracted experience.

Businesswise, what’s the goal of the website? Are you trying to monetize through clicks and ads, or is it ultimately about getting new subscribers?

The most immediate business goal of all Condé Nast websites is to generate print subscriptions. Having a website is much easier than sending out a lot of mail to people – especially younger people who don’t necessarily open mail. And the website has been a consistent generator of subscriptions.

We’re also trying to raise awareness of our stories and our magazine. We don’t post the whole magazine online and we keep an eye on what kinds of stories tend to do well. We’ve also seen more and more traffic for our online-only content.

We do a lot of thinking about what it means to be a magazine brand, and The New Yorker has one of the strongest brands in media. How do you take an 85-year-old institution and bring it into the digital age without compromising its identity?

It’s a really good question because if you had to come up with a list of adjectives for what the New Yorker brand represents – excellence, polish, depth – those aren’t necessarily things you can achieve on a blog, podcast or Twitter feed.

When we started the website the original plan was to fact check blog posts and that just doesn’t work. You can’t ask people to write in a freer, more immediate way and then put them through the same editorial machine. But New Yorker writers tend to have informal voices that are a lot more formal than most.

In terms of podcasts the revolution is that we’re able to take an office without windows, outfit it with a Mac, a couple of microphones, an M-Box and a phone box and operate at a very high level. We try to bring that sense of polished editing and excellence to things we can do simply but well.

Probably our biggest success on the site was a video of a man trapped in an elevator for 41 hours, which was a companion to a Nick Paumgarten piece in the magazine. I had gone to enough Web seminars where they say videos on the Web have to be less than three minutes long, so I handed off the elevator surveillance tapes to a multimedia producer and told her to cut it down by tomorrow. It became a big viral success and brought a lot of people around the world in to read an 8,000-word piece on elevators.

Who runs the magazine’s Facebook and Twitter accounts and how do you ensure they remain in line with the New Yorker brand?

Facebook and Twitter are joint ventures between our Web department and our public relations department. We joined Twitter fairly early on, before Ashton and Oprah. The New Yorker is all about cutting through the noise and telling people about the few things they should know. Our Twitter philosophy is very much the same: You put a couple of things out there a day, and only when they’re really important.

By far the best conversation about the Obama fist bump cover – in terms of diversity of opinion and civility – took place on our Facebook page. It was the kind of discussion your high school social studies teacher would be proud to have. But we’re not as informal or personal on Facebook or Twitter as some people have chosen to be. I don’t think anyone is tweeting from inside editorial meetings. That’s not the culture of this place, and I don’t think that would come as a surprise to anybody.

Does all this multimedia content merely expand the New Yorker brand experience for existing readers, or are you engaging people who might not read a 10,000 word article but will happily listen to an 11-minute podcast?

I think we’re doing both. Some of it is a generational question. For a 55-year-old reader, the idea that someone might both be interested in reading a 15,000-word piece about a shooting in Zambia and also be an active user of Foursquare is kind of anathema. But there are a lot of 25-year-olds who don’t see a contradiction between those things.

So in some ways we’re trying to cultivate the next generation of New Yorker readers. Some of it is giving people a taste of what they’re missing, some of it is supplementing the magazine experience, and some of it is about reaching a more international audience.

The New Yorker is not a magazine for everybody, but I think we have to make sure to reach the audience it can reach, and the Web is a great way of doing that.